2-[(6-Nitro-1,3-benzothiazol-2-yl)amino]ethan-1-ol | 78290-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-[(6-Nitro-1,3-benzothiazol-2-yl)amino]ethan-1-ol
• 英文别名: 2-[(6-nitro-1,3-benzothiazol-2-yl)amino]ethanol
• CAS: 78290-85-4
• 化学式: C₉H₉N₃O₃S
• 分子量: 239.255
• InChiKey: VDOWYVHDYDSPSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(6-Nitro-1,3-benzothiazol-2-yl)amino]ethan-1-ol 在 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以50%的产率得到N-(2-chloroethyl)-6-nitrobenzo[d]thiazol-2-amine
  参考文献：
  名称：

  Synthesis and In Vitro Antitumor Activity of Novel Fluorine Containing Pyrazoles and Pyrazolines

  摘要：

  研究人员合成了新型含氟吡唑（2a-2g）和吡唑（5a-5e），并使用磺基罗丹明 B（SRB）测定法对它们在体外四种人类癌细胞系中的细胞毒性进行了评估。尽管这些化合物在不同的细胞系中表现出不同程度的细胞毒性，但值得注意的是，4H 吡唑（5a-5e）对 MCF7 乳腺癌细胞系具有强效的选择性作用。

  DOI：

  10.2174/157018011797200812
• 作为产物：
  描述：

  2-氯-6-硝基苯并噻唑 、 C.I.酸性橙108 生成 2-[(6-Nitro-1,3-benzothiazol-2-yl)amino]ethan-1-ol
  参考文献：
  名称：

  DNA-damaging activity and mutagenicity of 16 newly synthesized thiazolo[5,4-a]acridine derivatives with high photo-inducible cytotoxicity

  摘要：

  The discovery of the potent anticancer properties of natural alkaloids in the pyrido-thiazolo-acridine series has suggested that thiazolo-acridine derivatives could be of great interest. In a continuous attempt to develop DNA-binding molecules and DNA photo-cleavers, 16 new thiazolo[5,4a]acridines were synthesized and studied for their photo-inducible DNA-intercalative, cytotoxic and mutagenic activities, by use of the DNA methyl-green bioassay, the Alamar Blue (R) viability assay and the Salmonella mutagenicity test using strains TA97a and TA98 with and without metabolic activation and photo-activation. Without photo-activation, one compound showed a DNA-intercalative activity in the DNA major groove while three compounds displayed intercalating properties after photo-activation. In the dark, four molecules possessed cytotoxic activities against a THP 1 acute monocytic leukemia cell line while 15 derivatives displayed photo-inducible cytotoxic activity against this cell line. All compounds were mutagenic in strain TA97a with metabolic activation (+S9mix) and 15 molecules were mutagenic in strain TA98 without activation (-S9mix). Study of the quantitative structure-activity relationships (QSAR) from the Salmonella mutagenicity data revealed that several descriptors could describe cytotoxic and mutagenic activities after photo-activation. From the results of the mutagenicity test, four compounds with elevated mutagenic activities were selected for additional experiments. Their, capacities to induce single-strand breaks (SSB) and chromosome-damaging effects were monitored by the comet and the micronucleus assays in normal human keratinocytes. Comparison of the minimal genotoxic concentrations showed that two compounds possessed higher capacities to induce SSB after photo-activation. In the micronucleus assay, three molecules were able to induce high numbers of micronuclei following photo-activation. Overall, the results of this study confirm that acridines are predominantly genotoxic via a DNA-intercalating mechanism in the dark, while DNA-adducts were probably induced following photo-activation. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.mrgentox.2007.10.022

文献信息

• In Vitro Activities of Position 2 Substitution-Bearing 6-Nitro- and 6-Amino-Benzothiazoles and Their Corresponding Anthranilic Acid Derivatives against<i>Leishmania infantum</i>and<i>Trichomonas vaginalis</i>
  作者：Florence Delmas、Carole Di Giorgio、Maxime Robin、Nadine Azas、Monique Gasquet、Claire Detang、Muriel Costa、Pierre Timon-David、Jean-Pierre Galy

  DOI：10.1128/aac.46.8.2588-2594.2002

  日期：2002.8

  6-Nitro- and 6-amino-benzothiazoles bearing different chains in position 2 and their corresponding anthranilic acid derivatives were investigated for their in vitro antiparasitic properties against parasites of the species Leishmania infantum and Trichomonas vaginalis compared to their toxicity towards human monocytes. Biological investigations established that the antiprotozoal properties depended

  研究了在位置2带有不同链的6-硝基和6-氨基-苯并噻唑及其相应的邻氨基苯甲酸衍生物在体外对婴儿利什曼原虫和阴道毛滴虫的寄生虫的抗寄生虫特性，以及它们对人单核细胞的毒性。生物学研究确定，抗原生动物特性很大程度上取决于位置2取代基团的化学结构。化合物C1，2-[（（2-氯-苯并噻唑-6-基）氨基]苯甲酸，对阴道锥虫物种的寄生虫表现出有趣的抗增殖活性，而化合物C11，2-（[2-[（2-羟乙基）氨基]-苯并噻唑-6-基]氨基）苯甲酸，以其胞内a节肢动物形式表现出对婴儿乳杆菌的寄生虫有希望的活性。